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Biblical “coolness” is counter-cultural. It looks remarkably different from how the culture defines and lives the cool life. The characteristics of biblical coolness are un-esteem, unlovely, unappealing, and unacceptable. (Read Isaiah 53:1-7) How do those descriptors grab you? Those are some of the things that describe Jesus. The irony of Christ’s out-of-step ways is how passionate Christians were about following Him.
I imagine that Jesus was more concerned about His schoolwork. I doubt He was interested in girls. His toga was perhaps a little out-of-date when compared to hip Jewish customs. His lunchbox probably had some of the animals from the Ark on it. Of course, He was the teacher’s pet, and His language was peculiarly different from His peers (John 7:46). Jesus was a real outlier.
As odd as He was, God chose Him to be our leader. It was not the mighty or the popular person. The chances of success ever coming His way seemed unlikely 1 Corinthians 1:18-25. What happens first: being godly or being cool? Those two words are competing against each other.
Jesus is amazingly cool. Don’t be fooled by what you see or what you crave. Do not succumb to the temptation to follow what our culture affirms as the way (John 14:6). Jesus is amazing. His path is the right one. The result of following the prototype for coolness will be eternally satisfying.